


On the Razor's Edge

by Waruitenshi



Series: Two Sides Same Knife [2]
Category: Supernatural
Genre: Altered Mental States, Alternate Universe - Supernatural, Angel Mojo, Angst, Angst and Humor, Angst and Hurt/Comfort, Angst and Romance, Bad Boys' Love, Blood, Blood and Gore, Bondage, Boys In Love, Breaking, Consensual Violence, Corruption, Dark Dean Winchester, Dark Fantasy, Dean in Hell, Demon Blood Addiction, Demon Deals, Demon Sex, Demons, Discipline, Disturbing Themes, Dysfunctional Family, Emotional Hurt/Comfort, Emotional Manipulation, Enemy Lovers, Family, Family Issues, Family Secrets, Fluff, Friendship/Love, Hell, Honesty, Horror, Hurt Dean Winchester, Imprisonment, Kidnapping, Language, Lima Syndrome, Love/Hate, M/M, Male Slash, Manipulation, Masochism, Master & Servant, Master/Servant, One Shot, Other, Pain, Painplay, Possessive Alastair, Possessive Behavior, Predicament Bondage, Psychological Horror, Psychological Torture, Psychological Trauma, Romance, Sadism, Sadomasochism, Sexual Content, Sexual Tension, Sexual Violence, Shounen-ai, Slash, Stockholm Syndrome, Suggestive Themes, Suicidal Thoughts, Supernatural Elements, Suspense, Teacher-Student Relationship, Threats of Violence, Twisted, Twisted Romance, Twisted and Fluffy Feelings, Violence, Yaoi, one shot series
Language: English
Status: Completed
Published: 2013-07-03
Updated: 2013-07-03
Packaged: 2017-12-17 13:36:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence, No Archive Warnings Apply
Chapters: 1
Words: 9,771
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/868161
Author URL: https://archiveofourown.org/users/Waruitenshi/pseuds/Waruitenshi
Summary: <blockquote class="userstuff">
              <p>Sequel to "Two Sides Same Knife". "You ask me to open that door and walk though it... you will not like what walks back out." He couldn't help smirking smugly at just how right Dean was! Because by the time Alastair was done, it would be something akin to Schrodinger's Cat as to whom was really the one getting tortured and who was doing the torturing… Alastair/Dean. Slash/Yaoi. One-Shot. Details Inside.</p>
            </blockquote>





	On the Razor's Edge

**Author's Note:**

> Hated how they killed off Alastair. He was one of my favorites! SO, I figured I'd fix that with this. Kuwahahahah!
> 
> Oh, I haven't seen Season 8 yet, so please no one spoil it for me, M'kay? X3 These are my thoughts on who and how I think Alastair is since his character wasn't all the delved into. 
> 
> Anywho! Yeah, this fic is based off of the episodes "Death takes a Holiday" and "On the Head of a Pin" along with a few references to others that Alastair was in, as I wanted to play around with the scene where Dean has to torture Alastair, and I think I put a fun twist on it. Especially the end! X3 
> 
> So, spoiler alert if you haven't seen those episodes and I must say that you should hurry up and watch them then! XD 
> 
> This is more of an insight on what I thought they felt with what went on and what I thought SHOULD have happened. XD So, like many fics, this one is pretty AU like the last one. LoL 
> 
> Dean is SO adorably conflicted and self-torturing! Always that internal struggle of who he wants to be and is happier being and who he thinks he should be based on what everyone TOLD him he should be. Good thing Alastair is there to guide him! Kuwahahah! Enjoy! :3
> 
> Now! ON WITH THE STORY! Please review! I find them tasty!

Unfortunately, now that Dean was out of Hell, the white-eyed torturer; as far as Lilith was concerned anyway, no longer had his rightful claim over the human. And so, had to resume his usual duties of trying to help break the seals now that the proverbial ball was recklessly rolling.

He wanted to go straight up to the human world and steal his hunter back and rip the wings off of the sanctimonious sky rats that took him in the first place! But, by the time he WAS allowed to go topside after having made a little deal with Lilith to give him incentive to break the seals, Dean seemed to be falling back into his old ways.

His hunter had crash landed back into that irksome state of denial, and for the sake of that bitch faced brother of his, was trying desperately to cling to it. Rather than embrace who and what he really was and be his boy again.

If it hadn't been for that tedious task of trying to kill those two reapers and break another seal, he would've had the boy back down in the pit, torturing souls by Alastair's side like he was meant to.

It had all been rather frustrating to be _so close_ yet so far. Dean was just on the other side of that chain barrier. Ah well, at least they got a little foreplay in with that shotgun he loaded up with rock salt.

It was more the sheer pleasure of finally getting to hurt that giraffe of a little brother Dean had though that helped make it more fun. Alastair _never_ liked that oafish twerp, and had no idea why Dean wasted the effort to care for someone who didn't even think the brunette was worthy of licking his boots. Alastair would let _his_ pupil spit and polish his shoes any time if Dean wanted to put his time to better use.

The demon really couldn't believe this moron was supposed to be Lucifer's metaphorical prom dress; even if he was just as annoying an eyesore as one of those stupid, puffy things.

It made the apocalypse just as unappetizing to the master torturer to as ever. He highly doubted anyone understood the repercussions of what they were trying to do; whether they were angels, demons, or humans that knew who picked a side.

Didn't they realize WHAT Lucifer was and what he thought of humans and demons? Hmn, then again, most of them hadn't originally shared a place with the former arch-angel in Heaven as Alastair had.

They hadn't been on friendly terms with Death himself and the Morning Star. Or been the one who taught Lucifer how to twist and break a human soul; the act that made Lilith into what she was (might be why she never liked him, but he disliked her anyway). Nor cast down with a chosen few who sided with Lucifer. Though, frankly he was more of a neutral party considering.

Alastair had only ever been interested in his studies. He could care less about their irritating politics. The reason he had been cast out of Heaven was mainly due to his having shared some knowledge that lead to the first demon being created.

Though, he supposed the fact that he'd found it entertaining and laughed when told probably hadn't helped his case. Ah well! He was never one to dwell on such and was just glad to be able to continue his arcane academics in a more comfortable realm. It had been a drafty craphole in the celestial plane anyway.

But getting to cause pain to that moronic moose sure helped to expel some of that pent up rage he had been saving for the angels when the time was right. And the situation was simply ripe for the picking since Sam couldn't get up his demon powers without a meat suit. It was just priceless!

Shooting that ghostly twit allowed Alastair a few seconds alone with Dean. Just enough to say the thing he'd been waiting to since the plan had been made in case the Winchester's showed up; and it was inevitable that they would you see. He approached the chain and he saw Dean shift closer on instinct. They stopped just close enough that they wouldn't touch it and he gave Dean that enigmatic yet oddly gentle smile like he did in rare times during their time together in Perdition.

"By the way…" Alastair began in sincere tone that took the hunter by surprise; Dean's name like honey on his lips. "It's good to see you again, _Dean_." Green eyes widened and his breath hitched as he frowned. He wasn't sure what to say to that… but, he couldn't help feeling the same, as much as he knew he should hate himself and the demon for it.

Irritatingly, Sam showed back up and so did the goody-goody Dean, before the real one he'd been trying to lure out could respond the way he should have. It was like the boy knew his brother was coming back. They did have that weird, brotherly connection, so it was to be expected. Or he could've been trying to be cautious about it.

Didn't want little Sammy seeing how close big brother and the mean ol' nasty demon were, hmm? Well, a bit _late_ for that probably… Not like Sam cared anyway. Alastair could tell that much just from first glancing the moose back when he'd been in that pediatricians body.

When the two denim wrapped nightmares managed to spoil the fun and save a seal, Dean thought he was free and clear. All he needed to do was find his brother and get them both back to their bodies before anything else horrible happened.

What he hadn't expected however, was Alastair showing up. Even if he had secretly hoped he'd see him again without anyone else around. Though _why_ he didn't want to think about or admit to right then.

But there he was; greeting him with that all too familiar Cheshire grin. His fingers lazily playing over the length of the black bladed scythe in his hand. "You can't run, Dean. Not from _me_." Alastair told him in an elatedly matter of fact way that filled him with dread of the truth it held.

It wasn't so much that Dean _couldn't_ run from him, so much as he really didn't _want to_. That was what made it so hard to process. The demon began to approach him slowly; the predator prowling closer to his doe eyed prey. Taking his time not because he had to, but because he wanted to.

Dean couldn't stop himself from backing away; his fight or flight beginning to kick in as he just knew he was in for a world of punishment before he'd be back on his masters good side. He'd been a bad little boy for staying away so long; no matter what his excuse may have been.

Even if the angels had been the ones to take him from Hell in the first place, Alastair would've reasoned he could've come back if he wanted to. And he HAD wanted to… but there was always something that held him back.

His remembrance of the promise he'd made to his dad to watch over Sammy, the fact that the idiot needed his protection now that he was trying to BFF that skank Ruby, and oh yeah, that little tidbit where the angels told him he had to save the world from the damn impending doom of the apocalypse!

So yeah, he was a wee bit tied up at the moment. Not that Alastair wouldn't tie him up on his rack again if he had voiced that. Instead, he wisely chose silence this time; his vocal cords paralyzed with fear and excitement anyway from being caught between old Dean and Dean from Hell.

"I'm inside that _angsty_ little noggin of yours." Alastair had continued speaking; and the boy hung on every word like a life raft in a raging sea. And he'd been _so close_! So very, painfully close! If he just took another step; a quick one that would've put him right up in front of his confused little hunter, he could've had him!

And in his fiendishly wanting state, he forgot all about those silly little sky rats with halos. He hadn't figured on them having the nerve to come near him really. So, it was an unpleasant surprise when he was struck by bright blue lightening and then whisked away from his green eyed prize to some dank, cold hole in the wall little prison to be tortured by those aggravating angels.

Not that their methods were very impressive. It was downright laughable in terms of how disappointing it was. His worst student could've done better with a popsicle stick and dental floss than they ever could if they had his best tools! Not that they did. The angels were mostly stuck using their powers; but they simply lacked the creativity to use them to his standards.

It was all rather boring really, and he was starting to think up ways to get out of his predicament. But when the master torturer heard his boy talking to that silly angel, he was pleasantly surprised as well as curious as to why they'd brought him here.

Hmn, seems they wanted his boy to torture him. This should be fun. And as he thought that, one part caught his attention the most. "You ask me to open that door and walk though it... you will not like what walks back out."

He couldn't help smirking smugly at just how right Dean was! Because by the time Alastair was done, it would be something akin to Schrodinger's Cat as to whom was _really_ the one getting tortured and who was doing the torturing…

It pained Dean almost as much as Alastair that he'd gone back to his old, heroic hunter ways, and it tore at him every time he had to see the demon. He felt even more lost, alone and despairingly wretched than he had before meeting Alastair. And it took every bit of waning strength to try and stay to take care of his brother and prevent the idiot from becoming Satan's bitch by leading his evil army.

At first, when he'd gone back to being alive, he really hadn't remembered anything from his years in Hell, so he was surprised when the angels made comments about it. But it steadily began to come back in the form of nightmares. At first, he didn't believe that he had really done all those things. But slowly he was forced to come to terms with reality because everyone haggard him to. Stupid, nagging angels… Though, Sam had been a LOT worse in his prying than anyone…

And after the initial shock and denial, soon he couldn't bare having the memories because they made him remember how close he and Alastair had been, which was an internal conflict of trying to decide whether or not that was such a terrible thing… So he did one of the things he did best. He pretended he didn't remember and tried not to think about it.

Instead, he threw himself into his work on cases, looking after Sammy, and drinking… lots and lots of drinking! It really sucked that the alcohol seemed unable to numb the type of pain he felt. This empty pit in his soul that he just couldn't seem to fill, no matter what he did.

And it worsened things when he always thought of the icy eyed demon whenever suffering or pain or blood, or any of the other associations he made with Alastair brought the memories flooding vividly back.

It was like a Hellish mixture of salt, rusty razors, broken glass and corrosive acid in an open wound when Castiel had the gall to ask him to torture his former lover and master. He wanted to run. He didn't want to be around the demon. Especially after having to hit him that one time to save that wishy-washy angel chick Anna.

But he had liked her he supposed… That short time they were together helped him to forget everything like one peaceful blackout. Which of course was ruined when he had to defend her from the one he _really_ wanted to be with. It made everything a thousand times worse.

The look of disappointment in those eyes was enough to churn his stomach and regret what he'd done. Dean wanted to take it back or even apologize. To put every single one of those aggravating angels on the rack and _show_ Alastair just how sorry he was by carving them into mutilated masterpieces that would bring back that approving smile the demon graced him with whenever he did a good job.

But as much as he wanted to avoid Alastair and hide in the darkest corner of the Earth, he had the staggering urge to see him. To be close to him again like they had been… So, using Castiel's plea for help as an excuse, Dean found his feet moving toward the object of his demented desires as he pushed the cart into the room.

It was a bit overwhelming to see Alastair bound in chains to a star shaped rack of his own. The sight brought back the nostalgia of when the demon thought it'd be fun every once in a while to let Dean have a go at him. To impress the chief torturer by seeing just what Dean could do to him.

Alastair could get as good as he gave and took such enjoyment in how Dean could give it. That was simply one of their fun little games they liked to play. At first Dean had been thunderstruck to find out just how much the demon enjoyed games. But he found it was abnormally adorable, considering who Alastair was and all.

For a demon, he played fair and by the rules; even if he was the one who made them. But even so, he wouldn't lie to Dean or try to find a loophole as he thought it was cheating. But that meant Alastair wouldn't let his lover do it either.

He was greeted by the demon chortling and eerily singing "I'm in Heaven", which tended to be one of the songs he used to sing in Hell to tease Dean when the other was about to start in on him. It was one of their _inside_ jokes so to speak.

" _Heaven_ , I'm in Heaven, and my heart beats so that I can hardly speak; and I seem to find the happiness I seek when we're out _together_ dancing, hmn, cheek to cheek." He sang impishly and swayed like he were really free to dance about; giving a jerk at his chains and leaning forward every so slightly as though offering an invitation for Dean to dance with him. Though, he really did want to get at the boy; for all the _wonderfully wrong_ reasons that he knew they'd both take pleasure in.

And Dean had to fight the smile twitching at the corners of his lips, because for the _tiniest_ moment before he remembered what he was here to do and his stony expression fell back in place, he didn't feel that gut wrenching emptiness…

Alastair watched him closely as always, and noticed how seriously the other was trying to hold his composure. It was utterly ridiculous to the white-eyed demon though. The angels sent _his_ star pupil to work _him_ over.

It was made all the more comical when he watched Dean pull the tarp off of his cart to see what the poor boy had to work with in terms of torture devices. His laugh a little wheezy from having been previously tortured by the angels; as pitiful as their attempts were.

As his mirth became too much to keep to himself, he decided to voice the thoughts he knew Dean shared. "Hmn, I'm sorry, this a very hmn, hmn, serious, very emotional situation for _you_. Ahem, I shouldn't laugh, it's just... I mean, _are they serious_? Hmn, they sent _you_ to torture _me_?" Icy eyes twinkled with irony.

Even the hunter couldn't help inwardly agreeing. But he just couldn't bring himself to voice it. Not after everything he'd gone through to try and regain his former self. To try and be the regular heroic and righteous happy-go-lucky big brother that Sam needed him to be. That he basically haggard him to be.

Sure they still had a lot to work out what with him finding out how his little brother was banging a devious little demon skank, but compared to what Dean had been doing in Hell, the brunette knew he had no moral high ground at all.

So it wasn't exactly like he could comment on Sam's actions or behavior. Nor all the lies Sam had been telling him. He just tried to pretend everything was fine and focus on cases and saving the world. It was what he did best… well, one of the things anyway. As far as Alastair was concerned, his talents lay elsewhere.

But life wasn't that simple sadly. Demons wanted to run amok and let the Devil himself out of his cage to destroy the world. And as much as he was sure Alastair had no interest in anything outside of Hell, that didn't mean those scumbag demons like Lilith were going to leave well enough alone.

So, for Sam, for Bobby, and everyone else who was counting on him to protect the world from demons taking over and wrecking the place, Dean had to put aside what he wanted as always and try to keep the world in one piece and his brother from leading Lucifer's army.

Dean took a deep breath and looked right at Alastair; his resolve wavering a little with how he knew the other was staring right into his soul. "You got one chance. One." He told the other gruffly. The other made a languidly lewd little "Oh." sound; urging him to say some more.

He always liked it when Dean got all _commanding_. His boy always was the fiery type and he could respect that. Even when his fire was burning and writhing brightly with passion beneath him. All bound and _sliced so finely_. Just begging to be taken. His tongue flitted out quickly to wet his dry, thin lips as he looked his appetizing apprentice over and found his hunger growing.

"Tell me who's killing the angels. I want a name." Dean did his best to look menacing as he knew he once did in Hell. And it only served to widen that amused and crooked grin the demon wore just for him.

"You think I'll see all your _scary_ toys and spill my _guts_?" Alastair saw how the cocky smile Dean tried to put on twitched because he was caught between wanting to laugh at the remark and positively terrified at the implications of what the angels wanted him to do to the demon. Because it wasn't like their little games in Hell… and it wasn't apart of the old Dean he was trying to recover… Or so Dean thought. But as always, Alastair knew better.

"Oh you'll spill your guts one way or the other. I just didn't want to ruin my shoes." Alastair's eyes surveyed the other from top to bottom again in a more obvious way and leaned forward daringly; jingling his chains in the process. "Oh, yeah…" The demon purred; his eyes twinkling darkly with wicked suggestion that made Dean suddenly get all flushed and his mouth become unbearably dry.

He wasn't mad at Dean for having to torture him. Hell, he had literally been in the same situation. Though it was for an entirely different purpose; albeit a stupid one as far as he was concerned. Seeing as he was fairly sure Lucifer would want to obliterate them all. But he doubted those fanatical morons on either side of the chessboard would've heeded his warnings.

"Now answer the question." Dean gave his slightly hoarse threat; which wasn't as intimidating as he would've hoped. "Or what? You'll work me over? But then... maybe...you don't _want_ to? _Maybe_ you're a-scared to?" He taunted the last bit in an eerie sing-song way that reminded Dean just how much better the demon was at this than he was, and Alastair relished every angst ridden moment of it.

"I'm here aren't I?" The brunette offered; his voice faltering as he tried to swallow the lump in his throat. His nerves were shot and he really wished he had some good hooch to chug and make this easier. Having to remember how he had been in the Pit was always made worse when he was around Sam or those angels.

In fact, he thought maybe, _just maybe_ he may have been able to deal with it if it hadn't been for Sam and Bobby, and those stupid freakin' angels. They made him feel ashamed, sickened to the core and like he should be horribly punished rather than "saved" by warriors of Heaven.

Simply sentenced to another forty years of torture. Though, compared to everything he'd gone through since coming back, he couldn't help how he thought it would've been a nice reprieve if Alastair was the one wielding the knife.

Everything he had been able to accept back down there, seemed to have been left there. And the master tormentor wasn't about to let him forget it either. "Not entirely. You left _part_ of yourself back in the Pit! Let's see if we can… get the two of you back together again, shall we?"

Dean felt a chill race down his spine at the silkily sinister way his former master said that and gulped. "You're gonna be disappointed." Alastair grinned and relaxed back against his restraints as Dean hurried to put some distance between them to go get the tools on his cart ready.

" _Oh,_ you have _not_ disappointed me so far." The demon drawled breathily; making that giddy pride Dean felt whenever praised by his teacher bubble up and get him all warm and fuzzy.

It made him hesitate for a moment and wonder briefly what would happen if he just let Alastair go and asked if he could go with him… Then felt his stomach twist in guilty knots for even considering. Yep, let the self-loathing commence!

Even if it had since the day he was pulled from Hell. Dean was walking on the razor's edge; a torturously tantalizing place the demon thought for him to be for the phrase rather suited his conflicted protégé. It was always intriguing to watch.

Quite the contrary in Dean's eyes though. He felt so unsure of everything lately… himself mostly, his role in the world now that he discovered that following in his dad's footsteps no longer was what he wanted or what made him happy. All the angels did was use and confuse him. Dean was even unsure of Sam…

The short silence that fell didn't irk Alastair as much as when he saw Dean hesitating and losing focus. He saw that resolve wavering and internal conflict smothering him, and knew that this wouldn't get him the results he wanted or that Dean needed.

"Come on, you gotta want a little payback for _everything_ I did to you. For all the _pokes_ and _prods_." He baited, but the stubborn hunter wasn't biting. The demon frowned slightly. If he was going to get the _real_ Dean back, drastic measures were required. The ones he'd used back in the Pit.

"Hm? No?" It didn't surprise him really. He knew how his boy felt about all of this. It was confusing for the brunette and without Alastair, he was lost. But the demon would help him find his way again. He just needed a little push. " _Um_ … How about for all the things I did to your _daddy_?" The look of shock he received from Dean slowly became engulfed by unadulterated hatred.

Yep! That was the right button! Family always _was_ a sore subject with his darling Deano. And it was one the demon could play to both their strengths. That fierce and fiery hatred he was feeling now would be what blossomed back into sadistic pleasure. Something which would easily bring his precious apprentice back to him; given he played this just right.

"I had your pop on my rack for close to a century" Alastair continued on conversationally; carrying on as easily as they did back in the pit. "You can't stall forever." Dean muttered gruffly; though more to himself than the demon as he fiddled with items on his pathetic trolley and as usual, Alastair paid him no mind.

"John Winchester. Made a good name for himself. A _hundred_ years. After each session, I'd, hmn, I'd make him the same offer I made you. I'd put down my blade if he picked one up." It bored Alastair to talk of the old twit, but it had to be done.

Dean could feel his hold on his sanity slowly beginning to slip. He didn't want to hear this… "Just give me the demon's name, Alastair." He warned; wondering how he could let the other get to him so easily.

' _Because he's always found a way to get under your skin…'_ His taunting inner voice told him; and he could hear the amused smirk in its words. But he knew it was right… Alastair literally knew him inside and out over their forty years together.

And as he fidgeted with what was in his hands, he did his best to block the demons words out; trying and wanting to believe they were just lies and all the sickening while knowing better.

"But he said "nein" each and every time." He watched aloofly as Dean took off his jacket; wondering if he simply didn't want to ruin it, or if he was starting to get all hot and bothered with anger. Hmm, probably a combination of the two no doubt.

"Oh, damned if I couldn't break him. Pulled out all the stops, but John... he was, well, made of something unique. The stuff of heroes. And then came _Deeeeaan_." The demon had always seemed to love saying his name and purred it slightly in an impish manner as he continued languidly.

" _Dean Winchester_. I thought I was up against it again. But daddy's _little girl_ , he _broke_. He broke in _thirty_!" Alastair wickedly chortled; unable to contain how much that fact delighted him to no end.

He was already getting to Dean. Just a bit longer… and then the boy would stop stalling and start slicing away at Alastair and this annoying façade he'd put up since leaving Hell.

"Oh, just not the man your daddy wanted you to be, huh, Dean?" And there it was! Dean had that look in his eye; the kind Alastair knew to mean he had struck a nerve and was about to pay for it. Oh how _exciting_!

Dean set his mind to the task and picked up a bronze chalice; moving it to where he needed it to be. "Hmn, now... Now we're getting somewhere." The demon breathed excitedly as he watched his pupil prepare. But then he frowned when he saw Dean pick up a jug.

"Holy water? Come _on_. Grasshopper, you're gonna have to get _creative_ to impress me." The white-eyed fiend all but growled in disappointment. But that's when it got interesting… well, more the kind he had been hoping and prodding the boy for.

"You know something, Alastair?" The brunette suddenly turned to him wearing a curious little smirk. Silencing the demon for once. "I could still dream, even in Hell." Hmm, well that was surprising… must've been during the times the kid blacked out when he went to make his reports. He made a note to keep future victims _entertained_ while he was away from now on as he continued to listen.

"And over and over and over, you know what I dreamt? I dreamt of this moment." A smile threatened to twitch on his face, but Alastair skillfully suppressed it. He'd need to keep a straight face and play along if he was going to have Dean jump off the deep end all on his own.

"And believe me... I got a few ideas." The dark and smirking way his apprentice said this however, gave him chills. Especially when he curiously eyed the other filling a syringe with holy water.

He watched as his boy plucked the bubbles out of the syringe and then approached him. That menacing little smile he used to wear when about to set in on a soul curving those pouty lips as he spoke. "Let's get started." Dean told him forebodingly. Hmn, well, maybe he hadn't left all of his true self back in the Pit after all…

And from there, it went quite well as far as Alastair thought. He groaned and screamed when the needle impaled his neck and injected him with that wretchedly purifying liquid; burning him from the inside out.

"Oh, man. Ooh." Alastair groaned breathlessly as he spat what he was sure was probably some of the now liquefied innards of his meat suit onto the floor. All the while Dean stepped back and turned to his table; trying to keep his composure but unable to keep that twistedly satisfied feeling of accomplishment from making him smile smugly at the other when he turned around.

"Let me know if you want some more. There's _plenty_ left." Alastair caught his breath, or was it that his meat suits vocal cords had been repaired? He didn't much care to think about it as such was a triviality.

"Go. Directly. To. Hell." He began darkly; for a moment, letting Dean think he'd gotten the better of the chief tormenter already. But then, his voice became the casual drawl it was before as he quickly added. "Do not pass go, do not collect $200."

Dean closed his eyes for a brief moment; the desire to roll them and leave the room for Alastair to rot there was very tempting. He really did hate how quickly that sinister spirit of his fell when he saw that yet again Alastair was the one with the upper hand. Smooth, sick, _sultry_ bastard…

Uh… hmm, he decided to let himself deny the sultry part; even if it did nag at him that it was how he felt. Dean's little smirk returned however when he remembered he did have at least one interesting tool in his arsenal to use, and went to fetch it.

The determined hunter picked up Ruby's knife and twirled it between his fingers more for show than anything; catching the demons attention despite the fact that he unknowingly always held it. "There's that little pig-poker. I wondered where it went." He commented with mild interest.

Dean ignored him and poured holy water over the silvery blade. But Dean wasn't the only one who would be poking and prodding here. "Do you really think this is gonna _fix_ you? Give you _closure_? Oh, hmn, that is _sad_. That's really sad. Sad, sad." Alastair smirked crookedly as he saw the hate twitching those handsome features.

Annnnnnd, in went the knife. Right into his gut. But with it, came that look of wicked ecstasy on Dean's face that he'd been waiting for when he gritted his teeth and the sound of sizzling hissed up from the wound. And oh how he couldn't resist dealing a blow of his own to his pupil.

"I _carved_ you... into a new animal, Dean. There is _no_ going back." He managed to grit out mockingly. Dean found himself looming closer to Alastair; until their faces were mere inches apart and reminded Dean of all those moments like this where their roles had been reversed and usually led to much more than torture that made his blood rush and his grin widen naughtily.

"Maybe you're right." Dean finally admitted; making his former teacher mirror his expression. It felt good to say it. Hell, it was liberating really. But now it was his turn to toy with the tormentor.

"But now it's my turn to carve." He added tauntingly as he gave the blade a rough twist; making the demon stiffen and bite back the scream that eventually clawed its way out and disturbed the angel in the other room even further.

However, as this went on… unbeknownst to any of them, a subtle squeak came from one of the knobs on a nearby pipe as it was turned just a tad by an unseen force… causing small drips of water to fall onto the chalk that made up the Devil's Trap that kept Alastair imprisoned on the rack.

Dean felt he was doing pretty well at how he was handling the situation. All the while never seeming to realize he was playing right into Alastair's hands and had already begun to sink back into his old torturing ways.

It just came _so easy_ … like breathing or driving his Impala. He didn't even notice it until he had gotten a lot closer to Alastair than he realized and found himself longing to swallow up those agonized screams and cries as he cut and stabbed into the demon.

Then, the demons head lolled forward and Dean grasped the others face with his hand so that they were eye to eye again. He needed to distract himself; needed to not relish or shiver ever so slightly at being able to touch his former master again.

Should be focusing on his task rather than how startlingly sexy Alastair always managed to look, even when a total mess. Sweat beginning to glisten on his pale skin as blood dripped down his chin and open wounds; staining the once clean sky blue shirt. Or how warm and welcoming he felt and how that hole in his soul was filling up with each passing second; especially the nearer they were.

The demons blood burbled laughing did at least help to snap him out of it a little and remember they weren't in Hell. "Now, it's your _professionalism_ that I respect." A little praise. Shocking and it almost made Dean smile. But he begrudgingly let go of the others face like he was disgusted with the demon, when it was really with himself.

Alastair could see all those pieces the other had tried to fit back together beginning to fracture as he grinned and spit his mouthful of blood; his mouth now stained crimson in a disturbingly alluring way that Dean tried not to look at while he clenched and unclenched his fists. He needed to do something to pretend he was "good ol' Dean" again. That he was doing the right thing like Castiel had told him earlier that he was.

He grabbed the chalice still filled with holy water and abruptly turned and threw it at Alastair; a good portion of it going into his bloodied mouth and down his throat as it began to steam and sizzle while he spluttered and tried to scream, but it just sounded like gargled groans.

"Who's murdering the angels?" He demanded as calmly as he could; his patience wearing thin as he mentally berated himself. Seemed the demon wasn't going to say anything.

So, Dean grabbed the jug and began filling the cup just enough to throw a few cupfuls at the demon; repeating the torturous process. Alastair had to admit, he was at least a persistent pupil. One of the many things he liked about Dean.

Once Dean was done tossing holy water at him, he unceremoniously spat what he hadn't ended up swallowing on the ground; wondering just how that Devil's Trap hadn't washed away yet.

"You're just not getting deep enough." He observed as he chided Dean like a good master does with his student when he wants to help him improve; his icy eyes going from the pink tinged liquid that had splashed on the ground back to his pupil. He had been talking about the holy water, but Dean couldn't help a twinge of irritation and arousal at the numerously implied meanings Alastair's words could hold.

He watched Dean exhale in aggravation and turn around to his cart. "Well, you lack the resources. Reality is just, I don't know, too concrete up here. Honestly, Dean... You have no idea how bad it really was…" Angry green eyes looked up from the salt he was pouring to the demon. "And what you really did for us."

The hunter didn't think that sounded very good. It never was when Alastair started like that. Especially with that crookedly enigmatic smile he had; like he knew all sorts of fun and frightening things Dean didn't. Which was true for a lot of reasons… "Shut up." He breathed hoarsely. Not wanting to know.

But where was the fun in that for the demon? "The whole bloody thing, Dean. The reason Lilith wanted you there in the first place." Before he knew it, his feet were carrying him back over and right up to the manipulative demon again. "Well, then I'll just make you shut up."

"Lilith really-" Alastair couldn't finish that thought though because Dean seized him by his face roughly and force-fed him salt. Making sure it got right down his throat! The demon began screaming and grunting again; choking on the burning salt as it turned those icy eyes white when they rolled back into his head.

Alastair gurgled and wheezed; trying to regurgitate the salt with much difficulty. It came up looking like a cherry slurpee that slopped onto the cold, hard ground. The demon coughed and tried to take a breath to speak; since those stupid meat sacks required it. "Something caught in my throat…" He frowned thoughtfully down at the ground where the reddish puddle gathered at his feet. "I think it's my throat."

Dean resisted the urge to laugh at this and merely made a little chuckling "Hm" sound. "Well, strap in because I'm just starting to have fun." Alastair returns the hunters smile with one of his own before he goes back to the trolley. Such a pitiful array of devices and tools really… but he supposed the kid wasn't doing bad considering what he had to work with.

"You know, it was supposed to be your father. He was supposed to bring it on. But, in the end, it was _you_." Another prod; like a dull knife pressing against the skin of his ribs and slowly cutting through the more pressure was applied that piqued the hunter's curiosity. Though he tried not to show it and just be nonchalant. "Bring what on?"

"Oh, every night, the same offer, remember? Same as your father. And finally you said, " _Sign me up_." Alastair continued on as if he hadn't heard him. The pressure growing with each word, until the remembrance of those three fatefully spoken words pierced right through and kept on cutting.

Alastair purred approvingly as he spoke just loud enough for Dean to hear if he strained a bit, so that the boy was focused almost entirely on his voice; whether he wanted to or not, which was debatable. " _Oooh_ , the first time you picked up _my_ razor... the first time you _sliced…_ into _that weeeeeping_ bitch…" Dean turned to look at the demon with stony bewilderment; wondering just what he was getting at.

Then Alastair grinned like the cat who ate the canary; his tongue flicking over his previously blood stained teeth from behind them. " _That_ was the first seal." It hit the hunter like a ton of bricks, but as he always tried to, he denied everything he knew and tried to hope that for once in his shitty existence that the other was being deceitful.

"You're lying." The smile was small and wavering. Alastair was rather offended at being called a liar; especially when Dean knew better. He puffed up and his white teeth bared menacingly. He looked rather intimidating; as if he were about to break free and rip the hunter a new one as he began to speak frightfully like those few times in the beginning of Dean's training when Alastair had disciplined his protégé for _really_ disappointing him somehow. Like Dean had just now.

"And it is written that the first seal shall be broken when a righteous man sheds blood in Hell. As he _breaks_ , so shall _it_ break." He gave Dean a moment and watched as the boy processed this. He couldn't believe what the demon was saying…

The young hunters mind was at war with itself yet again. It had to be a lie! It just had to… but, this was Alastair… He'd never lied to him before… Yeah, but that didn't mean he wasn't capable of it, right? The look the demon gave him made it clear he was being completely serious, as much as Dean wished he wasn't.

Alastair could see the shattering of the others mind and possibly his soul, and his smile faltered at the look on the boys face before Dean turned bitterly away from his former teacher. Unfortunately, he couldn't take _too_ much pleasure in the torment as he _did_ in his own disturbing way care for his boy.

"We had to break the first seal before any others. _Only way_ to get the dominoes to fall, right? Topple the one at the front of the line." He began to explain calmly; making sure the kid knew it was nothing personal as that was just his assignment, just like it had been Dean's to watch over Sam.

It wasn't like the master torturer had much choice since it was his boss who gave the orders. But again, it wasn't as if he hadn't enjoyed every excruciating moment of it anyway.

He could care less about the damn apocalypse, but if he was to hit the metaphorical heart of the issue, he needed to make it seem like it was a bigger deal than he thought it was. _Really_ sell it.

Which, ironically, what he said next still was quite honest. It was how almost all of Perdition thought and felt. "When we win... when we bring on the apocalypse and burn this Earth down... we'll owe it all to you... _Dean Winchester_." He said the others name as smoothly and fondly as if it were the sweetest nectar on his tongue. Dean did his best to stay still and not fall down and curl up into himself.

He was already shutting down mentally for the most part as he tried to sort out the gravity of Alastair's words. An unnerving quiet fell between them as Dean stood facing away from Alastair, who started to speak in a softer tone. Like he used to sometimes to Dean and only Dean back in Hell. "Believe me, son... I wouldn't lie about this."

The sincerity and familiarity of it tasted bittersweetly comforting to the hunter; who wasn't sure what to think of anything anymore. He needed to find something to ground himself, some lifeline to hold on to. And while he did that, Alastair couldn't help taking a bemusing notice in the soft, drip, dripping that was finally noticeable in the partial quiet of the room.

The Devil's Trap was now broken. "It's kind of a... religious sort of thing with me." The demon carried on as if the trap hadn't; even though his attention was wavering to the prospect of escape now being an option he needed to take while the hunter was distracted. And boy was he distracted.

He couldn't believe it. He felt used, betrayed… okay, he couldn't feel all that betrayed considering that he'd always felt there had been some hidden, evil motive behind his real reason for being in Hell. But even so! It wasn't like there was anyone else to be mad at and for him to take his frustrated feelings out on was there?

So, deciding to just swim around in a river of denial, he took a steadying breath and took solace in the only thing he could think of in his miserably angst-ridden state of mind. "No…" Dean breathed; his own voice sounding unsure but strengthening bit by bit.

"I don't think you are lying." He really didn't want to do this, not really. If he was being honest right now he would've acknowledged that he knew better. Should've came up with a different thought or decision, but if he was going to suffer, then why couldn't he drag the one he'd grown so close to right down with him.

It made some strange sort of sense to him that if he was going to break again why couldn't he have company. He felt lost and upset without Alastair, but also because of this revelation too. But at least he wasn't empty… not like he was sure his life might be if he didn't do what he planned to do next.

Just maybe though, if he succeeded, Dean could just end it there for both of them. He'd probably go back to the Pit, but who knew, maybe he'd find Alastair there waiting for him with a smile as sharp as his razor…?

That thought made him smile bittersweetly as he found his voice again. "But even if the demons do win…" It was now or never, and as shaky as his nerves were, he knew he'd have to. He gripped the knife in his hand; eyeing the blood. He was determined to use it to solve the whole dilemma. "You won't be there to see it."

However, as he turned around to "solve" his problems, he was completely shocked to see Alastair standing there with that razor smile just for him that he'd been thinking about moments ago.

But what both surprised and terrified him was that the tall, slender man was now standing there free and looking VERY amused. As if he knew every little anguishing thought that was tearing away at Dean's torn mind. Though, that much wouldn't be surprising he surmised.

"You should talk to your plumber about the pipes." The human possessing fiend muses smirkingly before punching Dean right in the face. Hitting him so hard, the boys face is so beautifully bloodied and broken. Hopefully it'd knock a little sense back into him.

Alastair took a deep, calming breath. Happy to be free and play with his boy toy again; it got his adrenaline pumping. He picked Dean up off the ground by the scruff of his shirt collar and began wailing on the shattered little heap of flesh; loving the pained cries he drew from the other, and the way the scarlet wetted skin broke and was further marred with each heavy blow.

Though, in reality, he was going easy on Dean. With the strength he possessed, he could've killed the kid with a single swing and not even have been making an effort. Alastair had fun watching how his human crumpled at his feet when he let him go. And how his eyes bugged out with sheer terror when he picked him back up by wrapping those spidery fingers around his throat.

He could easily snap it if he wanted to. But no, that wasn't any fun. At least, not right now. Carrying the hunter over to the rack as if he were his own personal rag doll, he slammed him roughly against it and held him there with a predatorily grin.

Alastair stared at the boy, _his_ boy, with the smug, sadistic satisfaction of a bug fanatic who was about to pluck the wings off of his irresistible little insect before dissecting him. It felt simply _too good_ to be dominating his protégé again.

"You got a lot to learn, boy. So I'll see you back in class... bright and early, _Monday morning_." His words were a mixture of menacing authority and honeyed affection that smoothed out near the end as he regarded the other while he tried to gasp for air.

Seeing the other such a writhing, defenseless mess was as stimulating as ever. Well, even more so now that it had been a while. It was like meeting alllll over again for the first time.

Which, reminded the master torturer with a glint of mischief in his icy eyes that Dean had been healed by the angels so that he was basically a virgin again. At least in the ways Alastair planned to defile him.

He hummed darkly as he leaned in to reclaim his well earned prize with a kiss, but was interrupted by someone pulling him around to face them! And as soon as he was spun, he knocked back the trench coat wearing nerd. Damn if he didn't hate those sanctimonious pricks!

But of course, the determined little angel was back on his feet in a flash and Alastair ended up dropping his prize to the ground as Ruby's knife was thrust into his chest; right near the heart his vessel had. Just barely missing it.

With an angry roar he slammed his hands against Castiel's chest; sending him flying backward. Dean, meanwhile was only conscious for a few minutes before he ended up blacking out. His last, albeit muddled, and not very coherent thoughts not very pleasant ones.

"Well, _almost_ …" The demon remarks as if a little impressed. "Looks like God is on my side today." The chief torturer quips smilingly as the knife sparks and sizzles in his chest. He does so enjoy how pissed off that made the little angel. At least, until the self-righteous little pigeon started twisting it in his chest.

Hmn, but the look on his innocent little face when the demon grabbed it and pulled it right out of himself was just downright photographable! Especially when he tossed it aside and lunged at Castiel like a sly beast.

They exchanged hits; most of them from a smirking Alastair who was winning easier than he should've; considering these were angels and all. You'd think they would've at least sent a better class of angel to handle him. It was almost insulting. But, he hadn't really had a good fight with an angel in a while. So, at least it was funny.

Alastair grabbed Castiel by that trench coat he ironically favored, and stuck him up on a pike that was sticking out of the wall; right between the shoulder blades and temporarily clipping his wings. "Well... like roaches, you celestials." He breathed; scolding the angel mockingly. "Now, I _really_ wish I knew how to kill you."

He pointed his finger at Cas scoldingly as the other struggled to get free from the spike in his spine and the hand crushing down on his throat like a boa constrictor. "But all I can do is send you back to Heaven." The demon quipped; wagging his slender digit at Castiel, and began chanting an exorcism to do just that!

As the demon recited the spell in Latin, Castiel's eyes and mouth began to glow a pure, blue-white light as his angelic essence was ripped from his body. Suddenly, there was a bright burst of light and then the human vessels eyes closed and Alastair relinquished the hand on the humans throat.

He left the human hanging there on the hook to die. The demon knew the angel would just heal his vessel and go back into it since for angels, meat suits were harder to obtain and needed to be cared for, but that wasn't any of his concern right now. There wasn't much time.

Alastair could care less about the angel wanting to throw a bitch fit when he got back, or the pointless war that waged between the two ethereal forces. He just wanted to take his apprentice and return to Hell to continue their studies together.

Which was why, he kneeled down beside the unconscious form of Dean. "Hmm… time to take you back home, my boy." He hummed roguishly while caressing the hunters cheek with the back of his fingers; smearing the lines of scarlet trickling down it.

For a moment he just reveled in having finally captured the stubborn brunette. Then, he picked him up and hoisted the human over his shoulder; grasping the knife beside him as he stood.

A look of surprise swept over his ruggedly handsome face when the double doors burst open; slamming against the concrete walls. He saw the youngest Winchester, Sam, barging in and couldn't help smirking.

He saw Sam pause in seeing that the master torturer was not only free but had his big brother resting on his shoulder like a sack of potatoes he planned on peeling. And not only that, but Castiel or at least the slowly dying man who he had originally occupied was groaning when he came too while he hung on the wall.

Wide eyes full of hatred, anger and corrupted by the power mad feeling Sam got from drinking demon blood stared at Alastair. The demons smirk widened and in a movement quicker than the human eye could make, he threw the knife in his hand and nailed it right into Sam's chest; piercing a lung but not killing him.

No, he knew better than to do that or Lilith might be a whiny bitch about it. But he could still make the oaf suffer. Sam collapsed onto his knees and then slumped on his side; trying and failing to catch his breath as a panicked look overcame him, and he realized he wasn't so high and mighty after all.

Humility… always interesting to see the demon mused to himself. "Sorry Sammy, but your big brother and I have a _whole lotta_ catching up to do." He remarked mockingly at the glower the overgrown moose shot him.

Sam raised his hand and made the face he always did when he was about to use his powers; that one that every demon and probably angel joked about how it made Sam look like he was severely constipated. Unfortunately for Sammy the twitlight vamp boy, Alastair thought it ironic to take a trick from the angels book and gave the knife a twist with his telekinetic ability.

Sammy wasn't the only one who had that particular power after all, but the demon was certainly the better one at using it. "Ah, ah, _aaaahh,_ kiddo. It's a _little_ late for that. But maybe, if you're a good little boy and obey Lilith, she might just let you visit Deano here down in the Pit. Though… frankly, hmn, I think he and I will be _too_ _busy_ , hmn, _playing_ for me to let him have any visitors."

The demon's tone was serious yet came off as wickedly mischievous. His spidery grip on _his_ apprentice tightened and those icy eyes turned to their true white that sparked with a dark possessiveness that Sam couldn't help but find freakin' terrifying.

And, with one last smug smirk that made the gasping heap of the wannabe hero scowl like it'd actually do something, Alastair vanished with Dean securely in his clutches! Leaving Sam to text Ruby to come pick him up and take him and Cas' vessel to the hospital before they both died.

Castiel of course would be back in his vessel and going to find Sam to figure out what happened before the hospital staff even had him in the emergency room. Needless to say, the angel was thoroughly confused when he awoke on that gurney while they were using the paddles on him!

All of Heaven was in an uproar at the fact that Dean Winchester had been taken back to Hell by the sly demon, and they would've laid siege to Hades again were they not lacking the numbers and power to do so.

Add to the fact that when Castiel went to go and investigate as to how exactly Alastair had gotten free, only to find that someone had let him loose on purpose, was very troublesome. Particularly since it was the angel Uriel who was behind the angel murders all along, and basically you had yourself one heck of a cluster fuck to deal with in the celestial planes!

The angels, specifically Castiel himself who felt responsible and guilt ridden for the whole fiasco, scoured the Earth many times over. But they never found anything that showed that Dean Winchester was still in the human realm…

The only thing he left behind to show he'd even existed had been his beloved Impala, his leather jacket, a worrying angel determined to find him, and a little brother who was steadily becoming so consumed and corrupted in his attempts to become stronger and better than his big brother that he'd stopped caring after the span of over a month with no signs of hope.

Other than that, you'd have never thought that a Dean Winchester had previously been apart of the living again… But one person knew. And he was the one who'd spirited the boy away to begin with. Right down into one of his favorite levels of Hell! But let's back up a little to when our twistedly lovely little couple arrived, shall we?

Alastair had gone through quite a bit of trouble bringing his precious prize back to Perdition. Lilith had given him a lot of heat over it, but he pointed out that the angels had _other options_ and that seemed to shut her trap. Besides, they had a deal and it wasn't like she could say much against it anyway. Like he even cared if she tried…

But he thought it was well worth it. Seeing as how he planned on making Dean repay him for all his hard work. And speak of the lil devil! The soft clinking of chains told him that his boy was finally awake!

The melodious, delicate sound bringing him out of that thoughtful state before focusing his impishly icy gaze on the sinewy, naked body bound before him on his rack. Just like it _should_ be…

Alastair felt a grin of sinister suggestion curving his cruel, thin lips at his next stream of thoughts about what he had been wanting to do to his darling Dean when he got him back. And now that he _had_ … _Oh_ , what a welcome home party this was going to be!

* * *

_**~The End… Of Part Two!~** _

**Author's Note:**

> DUN DUN DUUUN! LOL! Another cliffy! Well, sort of. XD I love making a series of One Shots. Don't ask me why, I just do. X3
> 
> Anywho! I hope I wrote the angsty, ever full of conflict, self-loathing and guilt ridden mess that IS Dean Winchester well. Lmfao. The fun part about Dean is that he tortures himself more than anyone probably ever could. I can see why Alastair thinks he so loveably fun. XD
> 
> SO, I think I delved in pretty well with Dean's time outside of Hell as I did with his time inside it. LoL And definitely improved the ending to "On the Head of a Pin". I hope you dear readers thought so too! X3
> 
> I'm already working on the third part of this series, and hope to cover even more of the complex Alastair/Dean relationship that they have, which should be interesting as this will be how I think the series might've gone had Alastair lived. Oh what fun! :D
> 
> Well, until my next fic, tootles you lovelies you! ;3


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